Daddy's Little Angel
by Aleisha Potter
Summary: "I know two things for sure, One: Bert and Ernie are gay, and two: you are not going to die a virgin, not on my watch".  Who could have known that such a simple statement could have such dire consequences.


A/N: okay, this has taken quite a bit of work. So many thanks to Stralude for ALL the help. Jude and Strom, you guys keep me sane... I have always love Castiel's character and after his trip to the "Den of Iniquity", this wouldn't leave me... It took a lot for me to be convinced to post this... it's such an odd and at times controversial pairing, yet I LOVE IT! Hope you enjoy it too... please, please, if you like it, review... I've been so hesitant about this, that I NEED the reviews for the courage to post the rest... Enjoy!

**Daddy's Little Angel**

**Part One**

Chloe stared at herself in the mirror. She wrinkled her nose in distaste at her clothing, if you could even call it such. Her top was a thin-strapped, slinky, thin white one piece that covered very little as it flowed down to her hips. Underneath the flowing, nearly see-through material, she wore a lacy, white thong and nothing else.

Why in all that was holy did she agree to do this for Lois? She always accused Clark of having a savior complex, but maybe she was wrong. Maybe that was her problem. She just didn't know how to say no.

Well, it was time she learned. After tonight, she was through. Let them find someone else to do the dirty jobs.

"Wow, Sidekick, you clean up nicely," Oliver told her, entering her room at Watchtower in his crisp, black Armani suit. "But, are you sure you should go wearing so… _little_?" he asked, his brow furrowed slightly.

She turned to face her boss, a glare firmly in place.

"Oliver, I'm supposed to be a hooker, what do you expect me to wear?" she asked, rolling her eyes. "And I'm not sure you should come with me. Imagine what that could do to your rep. if you're caught at a brothel."

"My reputation would survive, it's been through worse. Chloe, whenever anyone goes on a mission, you take back up. That's the rule, no exception. I'll stay out of sight, don't worry, but I'm not letting you go to _that _place alone."

"This isn't a JLA mission, this is a Lois mission."

"It's a mission. I'm going, get over it."

"Sir, yes, Sir," she snarked.

"Good, now that we're agreed, I'll follow you. Put your coat on and let's go."

* * *

Castiel sat across from Dean, nervously looking around the room. No matter where he looked, scantily clad woman graced his visage. Did Dean really expect him to participate in this indecent past time?

"This place is a den of iniquity. I should not be here," he told his friend, eyes widening as a tall brunette sauntered by, hips swaying in a tantalizing way.

"Dude, you full on rebelled against Heaven! Iniquity is just one of the perks!" the blond man told him with a smirk. "Now, I'm going to go find you the perfect girl so you can get this show on the road!"

Castiel watched the other man stand up and lumber off towards a few unoccupied women standing towards the back of the room. He glanced down at the cold beer Dean had insisted he consume, something about strengthening his resolve.

An odd feeling settled in his stomach, if he wasn't much mistaken, he would say he was nervous. He had felt many emotions in his short time with the Winchester brothers, but this kind of nervousness was new, and he wasn't sure he liked it.

He took a tentative sip of the beer and decided he actually liked it. Humans may have gotten one or two things right during their short existence.

Castiel sat his glass down as Dean approached the table, a short, blond woman in tow.

"Cas, this is Chloe, Chloe, Cas," Dean introduced the two.

The blond woman gave a nervous smile, her eyes darting around the room. Castiel's eyes strayed to her breasts, then widened as he realized how close her chest was to his face. He picked up his beer and gulped at it to cover his uncertainty.

"Hi," Chloe greeted, her eyes never meeting his. The angel swallowed twice, no words coming to his mind. What did one say to a woman who was offering you sexual intercourse in exchange for money?

"Well," Dean interrupted, causing Cas to jump slightly, "why don't you two kids go and enjoy yourselves, hmm?"

He watched the young woman's breathing pick up and her eyes go wide before turning around and walking towards the private exit in the back.

"Go, get her, Tiger."

Castiel slowly, nervously got up and began to follow her, but Dean stopped him.

"Here, give her this, if she asks for a credit card, tell her no. Oh! And stick to the basics, no ordering off the menu."

Castiel had no idea what any of that meant and he wasn't sure he wanted to find out. He took the pile of twenty dollar bills from his friend and made his way over to where the blond woman was waiting for him.

* * *

Chloe stood next to the door her "boss" had shown her earlier. "For the REALLY well paying customers," he had said. She had no idea what she was doing. She thought she could probably get away with simply lurking around the back until she caught sight of her target.

The other girls were tall, full bodied with legs that went on for miles, they were sure to be picked long before her. She was about to be proven wrong.

A blond man, taller than her but nowhere near as tall as Clark or Oliver, stopped directly in front of her. He was dressed down, casually and he wore a very comfortable looking leather jacket. She knew his type, she saw it quite often and she recognized his tactics, she saw Oliver use them all the time, but he did manage to surprise her.

"Hi there, darlin'. My name's Dean. What's yours?"

"Chloe," she answered, trying to aim for the light, breathy voice she often heard Lana use when talking to guys.

"Well, Chloe, I have a friend, a friend who you will absolutely love. The poor guy's been down on his luck lately, had an out with his family; I think he really needs some cheering up. I'll tell ya what; I'll pay you double, plus a little somethin' on the side if you can cheer him up."

Chloe's eyebrows rose in surprise. Reading between the lines, this guy sounded desperate.

She had to admit she was curious. She wondered what could possibly be wrong with his friend that he would need to one, find a girl _for_ said friend and two, pay sky high for the girl.

Chloe didn't know what to do exactly, but she knew if she refused to go, her cover would be blown and she couldn't afford that. Knowing it was her only option, she agreed to go with the blond man over to his table and meet his friend.

"Lead the way," she told him, pasting the most convincing smile she could on her face.

She decided that if it came to it, she could play along, get the man to one of the rooms then feign illness. She'd offer him any money he'd paid back, then make a hasty retreat, straight to the office to search for any files. Yes, that was the perfect plan.

The man, Dean she thought she remembered him saying, led her over to a small table that held a dark haired, very uncomfortable looking man. His eyes widened when they landed on her and she almost laughed. It was obvious he didn't frequent these places very often, if his insecurity was any indication.

Dean then introduced the quiet man as Cas, an odd name for a man she had to admit, but not the oddest she'd heard.

She allowed her eyes to roam the room, landing for a moment on Oliver and watched him raise a worried eye brow at her. She gave him what she hoped was a reassuring look before looking back down to Cas. He was guzzling at a tall glass of beer, looking a little pale; she moved her eyes before he could catch her staring at him.

"Hi," she said distractedly, begging someone to come and distract him from his obvious goal.

She heard Dean say something about having fun and took that as her cue to lead Cas to one of the back rooms. If she could just get through the next few minutes. She just had to make it look real.

* * *

Castiel followed the short blond woman down a narrow hallway and into a dark, musty room. He watched her flip on the light and survey the room. In one corner was a large bed covered in red silky material. There was scarce little else in the room. In another corner was a closed door. Cas had no idea where it might lead.

Before he could investigate, the woman, Chloe he had to remember to call her, spun around to face him.

"So. What… um, what can I do for you?" she asked, grimacing slightly. Cas wondered if all prostitutes acted as if their task was so distasteful. He handed her the waded up money.

"I believe I am supposed to ask you for promiscuity," he replied matter-of-factly. He watched her eyebrows rise.

"Uh, that is one way to put it, I suppose," she answered, taking the money from him and laying it down on the table nearest the door.

Castiel watched her move, wondering if he should follow her. She turned back to face him, her eyes made their way up and down his body before she tilted her head to the side.

"Are you okay? You… you don't seem to really want to be here. If your friend Dean is pressuring you to do something you don't want to do, then you can go. In fact, if that's the case, you should go," she told him.

"I am here of my own free will," he assured her, moving closer so he could look her directly in the eyes. "Tomorrow, it is very likely I will die and I don't wish to do so with my virginity intact," he explained.

He watched her eyes widen.

"Die? Are you in some kind of trouble?"

"Not yet, but I will be," he told her.

"Wait, did you say virginity?"

"Yes."

"You're telling me you've never been with a woman before?"

"No," he told her, unashamed of the fact, contrary to what Dean might think. He took another step closer to her, noticing that she was very agitated.

She had not ceased moving since they entered the room. Her eyes were very large and she constantly looked around, trying to take in everything while her breathing was fast and erratic.

"Are you okay, Chloe? You seem nervous. Is this your first time, too?" he asked curiously.

Her eyes widened even further than they had the last time.

"What?"

"I thought you might be nervous because this was a new experience for you as well," he explained, placing a hand on her shoulder and leaning closer. "I don't wish to make you uncomfortable."

Castiel couldn't help but notice Chloe's eyes were a very unique shade of green, similar to plants that used to grow in Eden, before the Fall and Lucifer's betrayal. So long ago.

He felt her breathing deepen as he leaned a little further in. A strange sensation was traveling through his body, settling not unpleasantly in his lower regions. He could feel a slight tingle where his palm lay on her bare shoulder.

Experimentally he moved his hand down her shoulder to her elbow and watched in amazement as small bumps erupted on her skin. He noticed his own breathing had increased and his heart rate seemed to be a bit faster than it was.

Her eyes were glazing over and he grew worried.

"Chloe?" he asked, making sure she was feeling alright.

"Hmm?" she replied, swaying closer to him. Every sensation he was feeling was heightened as her body came into the barest contact with his. He brought his other hand up and reached for her silky golden hair. It looked so soft; he just had to touch it.

Chloe leaned in to him and Castiel found himself cradling her head in his palm, her hair kissing his thumb and fingers. He leaned closer.

Having seen Dean kiss more than enough women, he had a pretty good idea of what he was supposed to do. Two small hands slid up his chest and he could see the hesitation on her face as she cupped the back of his neck. Slender fingers were relaxed yet she didn't seem to be, so he did what Dean would do and bent his head just a little, pressing his lips softly against hers.

His lower body grew taught, this time almost painfully so.

Chloe ran her tongue across his lips and he opened his mouth in surprise. Castiel gasped when her warm tongue slipped past his lips and pulled back in shock.

"You really are a virgin," she murmured.

Her breathing turned to a sharp gasp when his chest brushed hers and he glanced down, seeing two hard little tips showing through the delicate fabric. Curiously, he touched one and squeezed. Her gasp became an "Ow" and Chloe pulled back, her expression torn between laughter and shock.

"Easy there, tiger."

"That is the second time tonight I have been called that. Do I resemble a wild feline?"

Chloe raised a single eyebrow as she moved towards him, taking his hand and lifting it to her breast.

"Softer," she murmured, tilting her head for another kiss. "Softer."

Castiel swallowed hard, unsure if he should continue his exploration or not. Tentatively, he lowered his mouth to resume their kiss. He moved his hand over her breast again, this time being careful to caress her gently, as she instructed.

Chloe sucked in a breath at his ministrations and he was surprised to feel pride when she shuddered.

Moving his hand further down, he griped her hip tightly, pulling her body flush against his.

* * *

Chloe couldn't believe what she was doing. Surely she had lost her mind; she was making out with a total stranger, a stranger who had actually _paid_ her to do this! And worse, she was planning on going further with him!

She hadn't meant to, she really hadn't, but when he'd told her he was going to die tomorrow? She'd lost it. Her first thought had been that he needed a trip to the loony bin, but then he'd looked into her eyes, really looked, and she recognized something.

The look in his eyes was one she was familiar with. It was one she had seen many times, sometimes even in her own mirror. It was the look of a man who had seen enough, enough death, destruction and heart break to last a life time. She didn't know if he was really going to his death tomorrow, but he seemed to think so.

It didn't help that he was very handsome and so very, very innocent, at least when it came to women. His kiss had been full of naivety. She'd crumbled, and now she was seriously contemplating something very, very stupid.

She couldn't help it though! She was attracted to him, that was no lie, and in a very odd way, she saw herself in him when he looked deep into her eyes like that. She might regret this come morning, but for tonight? She would grant him his wish and make sure he didn't die a virgin.

She broke off the kiss once more, stepping slightly away from him, taking in his dazed expression. She carefully moved both straps off of her shoulders and allowed the flimsy negligee to fall to the floor.

His dilated pupils took in every inch of her nearly naked body.

She hooked her fingers into the thin straps of her lace panties and slid them off her hips and let them fall to the floor with the nightie.

Stepping out of the crumpled clothes, she took a step closer to him, hands reaching out to push off the heavy trench coat he wore.

Cas seemed to just stand there in a trance as she removed his jackets, tie and shirt, leaving him naked from the waist up. She leaned up to kiss him once again, this time pressing her naked breasts against his chest.

He inhaled sharply and wrapped his arms tightly around her. He seemed to finally be getting a handle on the kissing part. She brought one hand down and wrapped it around the bulge that was very present at the front of his pant.

He hissed and pulled back, eyes round and wide with shock. Chloe couldn't help but smirk at his expression. She stepped far enough back to unbutton and unzip his trousers, releasing his hard cock from its confines. She didn't think his eyes could get any wider, but they did.

His breathing was truly ragged now. It was eerie how he never seemed to blink as his eyes bored into her. She pushed his pants the rest of the way down, leaving them both naked.

He tentatively reached out a hand and lightly ran his fingers down her abdomen. Her eyes fluttered and she held her breath, watching his hand wander ever closer to the blond curls that hid her most private part. She sighed in disappointment when he let his hand fall before it reached its destination.

"I'm sorry, was that unpleasant?" he asked, his head tilting ever so slightly to the side.

"No, it was pleasant," she told him, fighting a smile at his bewilderment. "But you shouldn't have stopped."

Cas gave her a confused look.

Chloe reached out and grasped his hand, leading it to the cleft between her legs. She felt his fingers run experimentally across her wet folds. Pleasure tingled along her limbs, causing her to lean into him.

Haltingly, he allowed one finger to enter her tight warmth. The look on his face had turned to one of amazement. She moved her legs to grant him better access and sighed when she felt him add a second finger, gently moving in and out of her.

He stared down at her, as if he was trying to take in every inch of her, every expression.

Cas removed his hand from her and stared down at his fingers, a look of wonder on his handsome face.

Reaching out, she took his other hand and led him over to the bed. She prayed to anyone who might be listening that the sheets were at least clean.

Chloe lay down on the bed, pulling him down next to her. She noticed he was very stiff, every muscle tense, almost apprehensive. Wrapping a warm hand around his swollen cock, she kissed him gently, wanting to put him at ease. His first time should be a pleasant memory, not a nervous nightmare.

* * *

Castiel could hardly think. A part of him thought he should be outraged that she dare touch him the way she was, but then again, he had taken a great liberty when he had touched her and the majority of his mind and his very human body was eternally grateful for her hand and what it was doing. He could understand now why Dean attempted to bed every girl he met. If it was anything like this every time, perhaps it was not a bad way to live.

He felt bereft when her hand released him. He pulled back to request that she continue but before he could utter a word she pressed him onto his back on the bed.

He curiously watched as she moved one leg over him to straddle his body. She once again grasped him down there and seemed to position herself over him. He swallowed hard when he realized what she was going to do. His eyes locked with hers as she lowered herself onto him.

The sensations erupted around him in a way nothing had before. Everything exploded into ecstasy. She was so hot, as hot as the fires of Hell, but far more pleasing. He gasped at the feelings and emotions floating around him.

Castiel gripped her hips tight, raising his own at the last second to press as far as possible. Chloe moaned at his movement. Both sat completely still for a moment. It was becoming increasingly hard to process everything he was feeling and thinking.

Then Chloe started moving, very slowly up and down, and all thought left him. He was lost in the feeling.

She was heavenly… he mentally cringed at that analogy. Now he was even starting to sound like one of these humans.

Castiel gave up trying to think or rationalize anything. He just enjoyed the feeling of her sliding over him.

In no time at all, he felt a curious sensation. Something very different from anything he had felt before. He felt a dull ache begin in his lower body; his breathing and pulse went erratic. Chloe slowed ever so slightly and he almost called out, begging her not to stop. He desperately needed her to continue doing whatever it was she was doing that was causing this… _feeling_.

Suddenly, everything erupted. He felt his muscles coil, then explode, something hot and wet burnt in a wonderful way as it burst out of him.

"Holy Father!" he cried out as everything spun out of control, then darkness descended.

* * *

Chloe was breathing heavily as she watched him slip into unconsciousness. It wasn't surprising, even most seasoned men passed out after sex. It was perfect for her, the perfect opportunity to slip out and avoid the awkward post-coital discussion.

Slipping off the dozing man, she grabbed her clothes from the floor and quickly put them back on. She tiptoed over to the door but paused before exiting. Looking around, she saw the money he had given her for her services.

She suddenly felt sick when she realized she had actually slept with a man for money. There was no way she could live with herself if that was the case so she quietly went over to the table and picked up the waded bills. Moving over to his discarded clothes, she shoved the money into the pocket of his coat. This one was on the house; it would help her sleep at night.

After all, a one night stand with a stranger she could live with much easier than taking money for sex.

Chloe quickly exited the room and fled down the hall. She knew Oliver was somewhere still in the club and she worried that he might have panicked at this point and called in the cavalry. She did not need that tonight.

* * *

Castiel awoke to find himself strangely tired and… _satisfied_. It was a very good feeling he decided. Glancing around, he noticed that Chloe was gone, and so were her clothes. He had no idea if that was normal for this situation or not.

It didn't really matter, he supposed. He was unlikely to ever see her again. Was there such a thing as protocol when it came to women of the night? Perhaps he could ask Dean. Then again, maybe not.

He also found it odd that he had lost consciousness, how odd the human body was.

Grabbing his clothes, he quickly dressed and left the disheveled room. He walked down the long hall, pushing his hands into his coat pockets. His left hand encountered some waded up paper.

Curiously he pulled it out and was shocked to find the waded up money he had left for her. He was sure _that_ was not common. What a strange woman Dean had picked out for him.

Entering the main hall once again, he spotted his friend seated at a small round table, speaking animatedly with two tall, barely dressed woman. He walked over and tapped Dean on the shoulder. The blond man turned and his eyes widened when they landed on him.

"Cas! Whoa man, you actually went through with it?"

Castiel shifted uncomfortably. He felt warmth in his face at Dean's words. Averting his eyes, he quickly shoved the money back to his friend.

"Or maybe you didn't. Aw, come on Cas, tell me you didn't chicken out," he whined.

"I chickened out," the angel answered. For some reason, he felt that his experience was a very personal one and didn't want his exuberant friend to dissect it.

Cas watched Dean's eyes survey him before a smirk settled onto the other man's face.

"Oh, no, you didn't. You so did not chicken out. I know the look of a man who's been laid, Cas, nice try! But how did you get the money? That's a good one, even for you! Ha! Angel modesty, what a laugh," he clapped a hand on the angel's back and returned to his beer.

"Perhaps we should leave," he suggested, feeling very uncomfortable. "We should rest before facing Raphael."

"Yeah, you're probably right."

Dean threw a few waded bills down on the table, nodded goodbye to the two women and made his way towards the exit. Castiel followed silently, but paused when he caught sight of the blond woman he had been with earlier.

Chloe stood in a dark corner, a tall blond man stood beside her, his hand on her back while they faced a very angry looking, tall dark haired man. She seemed very upset and was arguing with the dark haired man.

The dark haired man said something that caused Chloe to pull her arm back and slap him across the face. He watched her pull away from the blond man and storm out the back entrance.

"Dude! I forgot how cute virgins were," Dean told him, slapping him hard on the back. Cas turned to his friend to find him smirking in the direction Chloe had gone.

"Let's go," the angel growled, leading the way out of the club, his face burning once again. He would never get used to these odd human reactions.

The two made there way over to the black Impala and Castiel was just opening the door when he heard loud arguing. He glanced up to see Dean listening, a worried expression on his face. He followed his friends gaze to find that same dark-haired man arguing with Chloe.

Castiel contemplated intervening, but Dean's negative jerk of his head convinced him otherwise.

"Let's go, Cas. Rough morning, remember?"

He nodded to his friend before lowering himself into the old, black car.

* * *

Chloe was furious. She was mad at herself, at Oliver, but mostly, she was mad at the arrogant Kryptonian that stood in front of her.

"Clark, just… go," she bit out, her breathing rapid from anger.

"You haven't answered my questions," he told her, leaning on her car door hard enough to prevent her from opening it.

"That's because it's none of your business."

"My best friend goes missing and I find her at a… a whorehouse, and that's none of my business?"

"No, it's not."

"Do you know how dangerous these places are! What were you thinking?"

"Oh, I don't know, maybe that I needed to get my kicks out before the world ends?"

Clark's face twisted into a look of disgust. Chloe rolled her eyes.

"Clark, for one, I wasn't alone, Oliver was in there…"

"Yeah, and that's supposed to make me feel better? You know how he is…"

"Clark! You know what? I've given you all the answers you're going to get tonight. Now, I am very tired, I have had a very rough day and my night hasn't been much better. My hand hurts from slapping you and I just want to sleep, so, please, just… get out of my way."

"Chloe-"

"Clark, move or I swear I will pull out the Kryptonite so fast…"

Clark sighed before moving out of her way, a resigned look on his face.

"This isn't over," he warned her.

"Oh, believe, me, I don't doubt it," she mumbled, folding herself into her car and starting the engine. As she pulled away, she glanced into her rearview mirror, Clark's scowling form shrunk as she pulled onto the deserted street and started on her way home.


End file.
